Biocidal benzylbiphenyl derivatives

Details Biocidal benzylbiphenyl derivatives Biocidal benzylbiphenyl derivatives

2000-09-22

2002-08-27

Aulakh, Charanjit (Department: 1625)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Biocides; animal or insect repellents or attractants

C546S191000, C546S223000, C546S229000, C564S316000, C504S248000, C504S306000

Reexamination Certificate

active

06440440

ABSTRACT:

The present invention is concerned with novel compounds of formula (I) having biocidal properties. The invention further relates to methods for preparing such novel compounds, compositions comprising said novel compounds as well as the use as a biocide for material and plant protection applications.
Micro-organisms are extremely useful, and even indispensable, in processes such as, e.g. alcoholic fermentation, ripening of cheese, baking of bread, production of penicillin, purification of waste water, production of biogas, and the like. However, micro-organisms can also be harmful or highly dangerous; by causing infectious diseases, by forming poisonous or carcinogenic metabolites and by attacking valuable materials, disturbing production processes, or impairment of the quality of products.
Biocides are a broad and diverse group of compounds which are able to kill micro-organisms or inhibit the multiplication of micro-organisms. Biocides can be classified as bactericides, fungicides, algicides, insecticides, acaricides, molluscicides, herbicides and the like. Well-known biocides are, for example, formaldehyde releasing compounds, phenol derivatives, salicylanilides, carbanilides, and quaternary ammonium salts. An extensive overview of biocides is given in “
Microbiocides for the protection of materials”,
by Wilfried Paulus, Chapman & Hall, 1st edition, 1993.
An important group of the biocides are the bactericides. Since bacteria occur everywhere, their destructive activity (biodeterioration) is basically unavoidable. Nevertheless materials can be protected with the aid of compounds that prevent the multiplication of bacteria at the relevant sites, either by killing them or inhibiting their development.
The present invention provides for novel compounds of formula (I) unexpectedly having biocidal activity. In particular, said compounds of formula (I) have bactericidal activity.
Structurally related compounds have been described in EP-0,219,756-A1, published on Apr. 29, 1987, having fungicidal activity.
The compounds of the present invention differ from the prior art compounds by the nature of the L moiety.
The present invention concerns compounds of formula (1)
stereochemically isomeric forms thereof, acid or base addition salts thereof, N-oxides thereof, or quaternary ammonium derivatives thereof,
wherein
the dotted line is an optional bond;
X is a direct bond when the dotted line represents a bond, or
X is hydrogen or hydroxy, when the dotted line does not represent a bond;
R
1
and R
2
are each independently selected from hydrogen, halo, hydroxy, C
1-4
alkyl, C
1-4
alkyloxy, nitro, amino, cyano, trifluoromethyl, trifluoromethoxy, C
1-6
alkylcarbonyl, hydroxycarbonyl, C
1-6
alkyloxycarbonyl, aminocarbonyl, di(C
1-4
alkyl)aminocarbonyl, C
1-6
alkylsulfinyl, C
1-6
alkylsulfonyl, aminosulfonyl, di(C
1-4
alkyl)aminosulfonyl, or —SO
3
H;
R
3
and R
4
are each independently selected from hydrogen, halo, hydroxy, C
1-4
alkyl, C
1-4
alkyloxy, nitro, amino, cyano, trifluoromethyl, or trifluoromethoxy;
R
5
and R
6
are each independently selected from hydrogen, halo, hydroxy, C
1-4
alkyl, C
1-4
alkyloxy, nitro, amino, cyano, trifluoromethyl, trifluoromethoxy, C
1-6
alkylcarbonyl, hydroxycarbonyl, C
1-6
alkyloxycarbonyl, aminocarbonyl, di(C
1-4
alkyl)aminocarbonyl, C
1-6
alkylsulfinyl, C
1-6
alkylsulfonyl, aminosulfonyl, di(C
1-4
alkyl)aminosulfonyl, or —SO
3
H;
L is a radical of formula
 wherein
A
1
is a direct bond or C
1-6
alkanediyl;
A
2
is C
2-6
alkanediyl;
R
7
is hydrogen, C
1-4
alkyl, phenyl or benzyl;
R
8
and R
9
are each independently hydrogen, C
1-6
alkyl, aminoC
1-6
alkyl or mono- or di(C
1-4
alkyl)aminoC
1-6
alkyl;
R
10
is hydrogen, C
1-6
alkyl, aminoC
1-6
alkyl or mono- or di(C
1-4
alkyl)aminoC
1-6
alkyl; and
R
11
is hydrogen, C
1-6
alkyl, amino, aminoC
1-6
alkyl or mono- or di(C
1-4
alkyl)aminoC
1-6
alkyl.
As used in the foregoing definitions halo is generic to fluoro, chloro, bromo and iodo; C
1-4
alkyl defines straight and branched chain saturated hydrocarbon radicals having from 1 to 4 carbon atoms such as, for example, methyl, ethyl, propyl, butyl, 1-methylethyl, 2-methylpropyl and the like; C
1-6
alkyl is meant to include C
1-4
alkyl and the higher homologues thereof having 5 or 6 carbon atoms, such as, for example, 2-methylbutyl, pentyl, hexyl and the like; C
1-6
alkanediyl defines bivalent straight or branched chain hydrocarbon radicals containing from 1 to 6 carbon atoms such as, for example, methylene, 1,2-ethanediyl, 1,3-propanediyl, 1,4-butanediyl, 1,5-pentanediyl, 1,6-hexanediyl and the branched isomers thereof; C
2-6
alkanediyl defines bivalent straight or branched chain hydrocarbon radicals containing from 2 to 6 carbon atoms such as, for example, 1,2-ethanediyl, 1,3-propanediyl, 1,4-butanediyl, 1,5-pentanediyl, 1,6-hexanediyl and the branched isomers thereof.
The term “stereochemically isomeric forms” as used hereinbefore defines all the possible isomeric forms which the compounds of formula (I) may possess. Unless otherwise mentioned or indicated, the chemical designation of compounds denotes the mixture of all possible stereochemically isomeric forms, said mixtures containing all diastereomers and enantiomers of the basic molecular structure. More in particular, stereogenic centers may have the R- or S-configuration; substituents on bivalent cyclic (partially) saturated radicals may have either the cis- or trans-configuration. Compounds encompassing double bonds can have an E or Z-stereochemistry at said double bond. Stereochemically isomeric forms of the compounds of formula (I) are obviously intended to be embraced within the scope of this invention.
The invention also comprises the salts which the compounds of formula (1) are able to form with organic or inorganic bases such as amines, alkali metal bases and earth alkaline metal bases, or quaternary ammonium bases, or with organic or inorganic acids, such as mineral acids, sulfonic acids, carboxylic acids or phosphorus containing acids.
Examples of salt-forming mineral acids are hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, chloric acid, perchloric acid or phosphoric acid. Salt-forming sulfonic acids are toluenesulfonic acid, benzenesulfonic acid, methanesulfonic acid or trifluoromethane sulfonic acid. Salt-forming carboxylic acids are formic acid, acetic acid, propanoic acid, butanoic acid, and the like. Salt-forming dicarboxylic acids are oxalic acid, malonic acid, succinic acid, glutaric acid, and the like. Salt-forming hydroxy acids are glycolic acid, lactic acid, malic acid, tartaric acid, citric acid, mandelic acid, and the like. Other salt-forming carboxylic acids are trifluoroacetic acid, benzoic acid, chloroacetic acid, phthalic acid, maleic acid, and malonic acid. Phosphorus containing acids are the various phosphonous acids, phosphonic acids and phosphinic acids.
Particular addition salts are acid addition salts obtained by treating the base form of compounds of formula (I) with appropriate acidic biocidal agents such as, e.g. 1,2-benzisothiazolone (BIT), 5-chloro-1,2-benzisothiazolone, 6-chloro-1,2-benzisothiazolone, 5-fluoro- 1,2-benzisothiazolone, 5-methyl-3(2H)-isothiazolone, or 4-bromo-5-methyl-3-isothiazolol. These addition salts can have different stoichiometry such as (1:1), (1:2), (1:3), (2:1), (3:1), (2:3) and so on.
Preferred salt-forming alkali metal hydroxides and earth alkaline metal hydroxides are the hydroxides of lithium, sodium, potassium, magnesium or calcium, most preferably those of sodium or potassium. Examples of suitable salt-forming amines are primary, secondary and tertiary aliphatic and aromatic amines such as methylamine, ethylamine, propylamine, isopropylamine, the four butylamine isomers, dimethylamine, diethylamine, diethanolamine, dipropylamine, diisopropylamine, di-n-butylamine, pyrrolidine, piperidine, morpholine, trimethylamine, triethylamine, tripropylamine, quinuclidine, pyridine, quinoline and isoquinoline. Preferred amines are ethylamine, propylamine, diethylamine or triethylamine,

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